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ChemicalBook > CAS DataBase List > 3-Morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one

3-Morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one

Description References
Product Name
3-Morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one
CAS No.
503615-03-0
Chemical Name
3-Morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one
Synonyms
5,6-Dihydro-3-(4-morpholinyl)-1-(4-nitrophenyl)-2(1H)-pyridinone;TECO-011;Apixaban int3;PR-204 impurity;Apixaban Impurity 19;Apixaban Intermediate3;Apixaban related impurities 1;5,6-Dihydro-3-(4-morpholinyl)-1-(4-;2-Naphthalenecarboxylicacid,12-amino-,methylester;5-morpholino-1-(4-nitrophenyl)-2,3-dihydropyridin-6-one
CBNumber
CB62516219
Molecular Formula
C15H17N3O4
Formula Weight
303.31
MOL File
503615-03-0.mol
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3-Morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one Property

Boiling point:
506.5±50.0 °C(Predicted)
Density 
1.356
storage temp. 
Sealed in dry,Store in freezer, under -20°C
solubility 
Chloroform (Slightly), Methanol (Slightly, Heated)
form 
Solid
pka
3.11±0.20(Predicted)
color 
Light Yellow
InChI
InChI=1S/C15H17N3O4/c19-15-14(16-8-10-22-11-9-16)2-1-7-17(15)12-3-5-13(6-4-12)18(20)21/h2-6H,1,7-11H2
InChIKey
LBFAEOWNWSDWRZ-UHFFFAOYSA-N
SMILES
C1(=O)N(C2=CC=C([N+]([O-])=O)C=C2)CCC=C1N1CCOCC1
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

TRC
Product number
M725125
Product name
3-(Morpholinyl)-N-(4-nitrophenyl)-5,6-dihydropyridin-2-one
Packaging
5g
Price
$745
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
CHM0389374
Product name
3-MORPHOLINO-1-(4-NITROPHENYL)-5,6-DIHYDROPYRIDIN-2(1H)-ONE
Purity
95.00%
Packaging
5MG
Price
$497.13
Updated
2021/12/16
ChemScene
Product number
CS-M1442
Product name
3-morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one
Purity
99.68%
Packaging
100g
Price
$780
Updated
2021/12/16
ChemScene
Product number
CS-M1442
Product name
3-morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one
Purity
99.68%
Packaging
5g
Price
$75
Updated
2021/12/16
ChemScene
Product number
CS-M1442
Product name
3-morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one
Purity
99.68%
Packaging
10g
Price
$125
Updated
2021/12/16
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3-Morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one Chemical Properties,Usage,Production

Description

3-(4-Morpholinyl)-1-(4-nitrophenyl)-5, 6-dihydro-2(1H)-pyridinone is the intermediate for the synthesis of apixaban, which is an anticoagulant for the treatment of venous thromboembolic events. 

References

Chao, H. E., et al. "Synthesis of Apixaban." Chinese Journal of Pharmaceuticals (2014).
https://en.wikipedia.org/wiki/Apixaban

Chemical Properties

5,6-Dihydro-3-(4-morpholinyl)-1-(4-nitrophenyl)-2(1H)-pyridinone contains a nitro unit and a morpholine group in its chemical structure, which has excellent chemical reactivity and poor chemical stability, and the double-bonded unit in its structure can be reduced by hydrogen under certain conditions. Hydrogen reduction usually requires appropriate catalysts and reaction conditions.

Uses

3-(Morpholinyl)-N-(4-nitrophenyl)-5,6-dihydropyridin-2-one is a reagent in the synthesis of 4,5-dehydro Apixaban (D229385) an impurity of Apixaban (A726700), a potent, direct, selective, and orally active inhibitor of coagulation factor Xa. It is a potential new oral coagulant that may be useful prevention of venous thromboembolism in total hip, knee replacement orthopedic surgery and stroke in treatment of patient with venous thromboembolic disorder or with atrial fibrillation

Synthesis

110-91-8

38560-30-4

503615-03-0

The reaction mixture was quenched with 1-(4-nitrophenyl)-2-piperidone (33 g, 0.15 mol) and phosphorus pentachloride (109 g, 0.52 mol) by slowly pouring into 500 mL of ice water. The aqueous layer was separated and the aqueous phase was extracted with chloroform (3 x 100 mL). The organic phases were combined and the reaction mixture was extracted with ethyl acetate. Subsequently, the combined organic phases were washed once with 500 mL of saturated sodium chloride solution and dried with anhydrous magnesium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure to give 57 g of a yellow solid. The solid (57 g) was placed in a reaction flask, morpholine (307 mL) was added, slowly heated to reflux, and the reaction was maintained for 2 hours. Upon completion of the reaction, it was cooled to room temperature and the morpholine hydrochloride solid precipitated. 600 mL of water was added to precipitate the product, and the yellow solid was collected by filtration and dried to give 30 g of the target compound 5,6-dihydro-3-(4-morpholinyl)-1-(4-nitrophenyl)-2(1H)-pyridinone in a total yield of 66% for the two-step reaction.

References

[1] Patent: CN103626689, 2016, B. Location in patent: Paragraph 0033; 0044-0046
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 22, p. 5339 - 5356
[3] Patent: US2003/232804, 2003, A1. Location in patent: Page 102
[4] Patent: US2003/232804, 2003, A1. Location in patent: Page 96
[5] Patent: WO2014/203275, 2014, A2. Location in patent: Page/Page column 35

3-Morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one Preparation Products And Raw materials

Raw materials

Preparation Products

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3-Morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one Suppliers

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View Lastest Price from 3-Morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one manufacturers

Wuhan Biocar Pharmacy CO.,Ltd.
Product
3-Morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one 503615-03-0
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
600kg
Release date
2025-03-12
Speranza Chemical Co., Ltd.
Product
3-(4-Morpholinyl)-1-(4-nitrophenyl)-5,6-dihydro-2(1H)-pyridinone 503615-03-0
Price
US $25.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
20 tons
Release date
2019-12-24
Jinan Million Pharmaceutical Co., Ltd
Product
3-Morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one 503615-03-0
Price
US $2.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1200KG/M
Release date
2023-08-15

503615-03-0, 3-Morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-oneRelated Search:

ethyl 6-(4-aMinophenyl)-1-(4-Methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate 5-chloro-N-(4-(5-morpholino-6-oxo-3,6-dihydropyridin-1(2H)-yl)phenyl)pentanamide Acetic acid, 2-chloro-2-[2-(4-methoxyphenyl)hydrazinylidene], ethyl ester 3-Morpholino-1-(4-(2-oxopiperidin-1-yl)phenyl)-5,6-dihydropyridin-2(1H)-one 1-(4-AMinophenyl)-5,6-dihydro-3-(4-Morpholinyl)-2(1h)-pyridinone 1-(4-Methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester 1-(4-Nitrophenyl)-2-piperidinone 4,5,6,7-Tetrahydro-1-(4-methoxyphenyl)-6-[4-(5-methyl-2-oxo-1-piperidinyl)phenyl]-7-oxo-1H-pyrazolo[3,4-c]pyridine-3-carboxamide 1-(4-Methoxyphenyl)-6-(4-(2-Methyl-6-oxopiperidin-1-yl)phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxaMide Apixaban IMpurity 6 1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid Apixaban Impurity 12 Apixaban 1-(4-chlorophenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxaMide 1-(4-Methoxyphenyl)-6-(4-iodophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester Apixaban IMpurity 3 Apixaban Impurity 17 Apixaban IMpurity 4 (BMS-728626-01)

  • 3-(4-Morpholinyl)-1-(4-nitrophenyl)-5,6-dihydro-2(1H)-pyridinone
  • 5,6-Dihydro-3-(4-morpholinyl)-1-(4-nitrophenyl)-2(1H)-pyridinone
  • Apixaban Intermediate3
  • 5-morpholin-4-yl-1-(4-nitrophenyl)-2,3-dihydropyridin-6-one
  • 3-(Morpholin-4-yl)-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one (Nitro MPDP)
  • 3-Morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one
  • Apixaban Impurity 19
  • 5-morpholino-1-(4-nitrophenyl)-2,3-dihydropyridin-6-one
  • 5,6 - dihydro-3 - (4 - morpholin-yl) -1 - (4 - nitrophenyl) -2 (1H) - pyridone
  • 3-(Morpholinyl)-N-(4-nitrophenyl)-5,6-dihydropyridin-2-one
  • Apixaban int3
  • Apixaban related impurities 1
  • 2(1H)-Pyridinone, 5,6-dihydro-3-(4-morpholinyl)-1-(4-nitrophenyl)-
  • Apixaban intermediates，5,6-Dihydro-3-(4-morpholinyl)-1-(4- nitrophenyl)-2(1H)-pyridinone
  • 5,6-Dihydro-3-(4-morpholinyl)-1-(4-nitrophenyl)-2(1H)-pyridi...
  • Morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one
  • 2-Naphthalenecarboxylicacid,12-amino-,methylester
  • TECO-011
  • 5,6-Dihydro-3-morpholino-1-(4-nitrophenyl) pyridine-2(1H)-one
  • 1-(4-Nitrophenyl)- 3-Morpholin- 4-yl-5,6- dihydopyridin- 2(1H)-one
  • PR-204 impurity
  • 3-(morpholin-4-yl)-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one
  • 3-(4-MORPHOLINYL)-1-(4-NITROPHENYL)-5,6-DIHYDRO-2(1H)-PYRIDI 99%min
  • 5,6-Dihydro-3-(4-morpholinyl)-1-(4-
  • 3-morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one (Intermediate of Apixaban)
  • 503615-03-0
  • 503615-03-0